View of Downtown and South Shore Marina from South Shore Park

The Grant Park Beach – Oak Leaf Trail — Shore line loop from South Milwaukee offers a wonderfully accessible touring cycling experience, tracing the picturesque Lake Michigan shoreline. You will glide along predominantly smooth asphalt paths, winding through the historic Grant Park with its towering bluffs and deep ravines, and past the tranquil Oak Creek Parkway. Expect refreshing lake breezes and a mix of dense woodlands and open green spaces, with opportunities to spot local wildlife, making for a truly engaging ride.

This easy 16.4-mile (26.5 km) loop, with a modest 424 feet (129 metres) of elevation gain, can be completed in about 1 hour and 33 minutes, making it suitable for most touring cyclists. While generally flat, be prepared for a few gentle undulations, including a scenic descent near Bay View Park. The route is well-supported with amenities like restrooms and concessions available in parks along the way, so you can easily plan your stops.

As an integral part of the 135-mile Oak Leaf Trail system, this loop provides a fantastic entry point to Milwaukee County's extensive multi-use paths. You can even connect to the famous Seven Bridges Trail within Grant Park for a short hiking detour, known for its unique covered bridges and peaceful nature paths. This route is a great option for families or anyone looking for a relaxed ride with high scenic payoff and easy access to local parks.